The Human Potential Project

Celebrating Failure A Success

Five years ago, Cassandra Phillipps founded FailCon, a one-day conference in San Francisco celebrating failure. Discouraged by a growing chorus of start-up founders promoting their triumphs throughout Silicon Valley, and nervous about her own prospects as an entrepreneur, she craved the stories of people who had flopped. The conference was a success. And every October for the next four years, up to 500 tech start-up newbies have gathered with industry veterans who dish on their “biggest fail” and lead round-table discussions with titles like “How to Conduct Yourself When It All Goes Off the Rails.” But this year, the FailCon event in San Francisco was canceled, and Ms. Phillipps says part of the reason is that failure chatter is now so pervasive in Silicon Valley that a conference almost seems superfluous. “It’s in the lexicon that you’re going to fail,” she says.

In her five years running FailCon as a side project while holding down other full-time jobs, Ms. Phillipps gathered a fair amount of entrepreneurial wisdom. In her current job as a game designer for the mobile gaming company Pocket Gems, she says she always assumes that new products her group creates will hit the skids in several ways. They will discover a problematic employee in the mix, for example, or the products will garner some negative user reviews. “There has never been a product launched that didn’t have those failures,” she says. Ms. Phillipps and her team pre-emptively draft plans for how to handle these and other problems. They brainstorm specific solutions and set up warning systems to clue them in to the fact that a fiasco has occurred in the first place.

In some ways, FailCon’s success created a quandary for Ms. Phillipps. The last three conferences sold out, each drawing 400 to 500 people who paid $100 to $350 each. And FailCon attracted big-name sponsors, including Amazon Web Services, Comcast and Microsoft. She says the conference was financially profitable. Now, she says that Silicon Valley’s embrace of failure has outgrown the FailCon format — and that a one-day conference no longer seems to be the best fit. So she is aiming to reboot FailCon. She may turn to smaller, more interactive workshops and an invitation-only application process. FailCon 2.0 is to make its debut in October 2015.